Boston checks all the traditional boxes for solo travel—it’s safe, culturally rich, and accessible—and offers innumerable, unexpected reasons to visit on your own. The New England hub has been named the safest city in America on several occasions, and public transportation via train or rail is easy and among the most affordable in the nation. There’s also perhaps no better way to explore the city’s 23 diverse neighborhoods than on foot. Boston’s compact nature makes it an exceptionally walkable city. You can retrace colonists’ footsteps in the North End and marvel at one of the country’s most modern skylines in the Seaport District, all in an afternoon.
This diversity of experiences parallels a diversity of thought as well. Boston is a true collegiate city, with some of the world’s leading universities attracting scholars from around the globe. The students at these institutions give the Massachusetts capital a youthful perspective that’s particularly welcoming for independent travelers. From academia to athletics, here’s why Boston is the perfect destination for solo explorers in wintertime.
See fine art and attend museum events
Boston’s collection of art museums is reason enough to plan a city visit. Solo-friendly nights at the Museum of Fine Arts, the Institute of Contemporary Art, and the Harvard Art Museums (located just across the Charles River) pair enriching culture with a party, cocktails, music, and great conversation.
Among the most enchanting are the wintertime First Thursdays at the Isabella Stewart Gardner Museum, where a lush indoor garden that flourishes year-round is just as beautiful as the Roman, Gothic, and Renaissance architecture of its buildings. The former home and gallery of a wealthy widow, it transports visitors to the early 1900s and is now one of the country’s finest independent collections of portraiture and Dutch Masters.
Go ice skating or attend a sporting event
Boston’s outdoor rinks don’t disappoint.
Courtesy of Meet Boston/Ed Wonsek
Boston also has ample opportunities for sports enthusiasts and active travelers. The city has won 13 professional championships in the 21st century, including those of its winter home teams, the NHL’s Boston Bruins and the NBA’s Boston Celtics. Both compete for glory at TD Garden in the heart of the city. Single tickets are often available at a discount at the last minute. (Pro tip: Design your own three-course feast from 18 local restaurants at the on-site Hub Hall food market.)
The city’s outdoor ice-skating rinks are another way to get the blood pumping. Lace up at Boston Common Frog Pond, Kirrane Rink in the Brookline neighborhood, or at South Plaza in Cambridge.
Visit independent bookstores in Back Bay, South End, and Beacon Hill
You’ll find independent bookshops in almost every Boston neighborhood, including Trident Booksellers & Cafe in Back Bay (a historic district that’s also a paradise for historians and shoppers). The bookstore More Than Words in South End is a nonprofit that employs disenfranchised youth and teaches them business skills. For those who like food with their thoughts, Beacon Hill Books & Cafe in Beacon Hill has one of the city’s most charming cafés and tea services. The historic former home’s crackling fireplaces are cozy on snowy days.
Get coffee at cozy cafés
Warm up and check out some of Boston’s best mom-and-pop shops at an independent coffeehouse. Beantown-based roaster George Howell has several locations. Two in particular make for a great start to a day of solo exploring: Downtown Crossing is in the heart of the city and Boston Public Market has city-centric eats, arts, and programming (events include trivia nights and live music). To discover one of Boston’s other lesser-explored neighborhoods, Recreo Coffee & Roasterie in West Roxbury makes a great jumping-off point or a spot to simply curl up and read.
Eat, drink, and be merry at a pub or fireplace restaurant
Of Boston’s many legacies, one of its most well-deserved is its craft beer scene. Harpoon was the first of many in the Seaport District, where you can also spend the greater part of a day checking out Trillium. The neighborhood’s buzzy energy and restaurants make it a draw for solo travelers.
Other great independent dining options, especially in winter, include Bar Vlaha in Brookline, where the open flame and ambiance of a Greek kitchen create a cozy vibe and friendly atmosphere. You can warm up at restaurants with fireplaces across the city, many of which are expected to make the Michelin list in Boston’s first year as a designated Michelin city. Honors are still rolling out this fall, so subscribe to Meet Boston for updates, including those about Dine Out Boston, a multiweek event featuring three-course prix-fixe menus at some of the city’s hottest restaurants.
Go dancing at a rock club
Night owls, rejoice—entertainment after dark is what dreams are made of for solo travelers in Boston. You can hear live music and DJs most nights of the week at Big Night Entertainment clubs such as Royale. Or hop on the Red Line to hit up the Middle East Restaurant & Nightclub in Cambridge for bands, dancing, and dinner. As home to several of the country’s best music universities (including John Mayer’s alma mater, the Berklee College of Music), a live music scene thrives at smaller independent venues like the Brighton Music Hall, Paradise Rock Club, and the Sinclair.
Celebrate the season at a craft market or festival
This year, SoWa Winter Festival celebrates its 10th anniversary of crafts, craft cocktails, and live music in the South End.
Courtesy of SoWa Power Station/SoWa Winter Festival
In Boston, winter festivals highlight all things cozy, festive, and local. SoWa Winter Festival is a month-long opportunity to enjoy hands-on workshops, sip craft cocktails, pick up souvenirs or gifts, and hear live music. Snowport turns the Seaport District into a glowing open-air holiday market with curling, pop-up shops, and warm cocktails. First Night Boston kicks off the new year with festivities such as fireworks, an ice sculpture walk, and a parade.
Relax at spas in the heart of the city
One of the best parts of solo travel (especially in wintertime) is the uninterrupted opportunity to relax and restore. The Moki sauna village pop-up experience features Finnish-style wooden cabins and cedar cold plunge barrels in the center of the city. (The location of the villages rotates, so subscribe to Meet Boston for ongoing updates.) Another serene relaxation experience is at the Omni Boston Hotel at the Seaport, where steam rises from the rooftop’s heated pool and hot tub as snowflakes fall gently around you.
Go on a historical or culinary walking tour
The North End, Boston
Courtesy of Meet Boston/Kyle Klein
Try a winter walking tour in Boston that pops in and out of places to warm up. You can get your lunch with a side of history on an Off the Eaten Path tour in the North End. Before it became Boston’s version of Little Italy, Paul Revere made history here. His home and the church of the revolutionists come to life with the story of the immigrants who followed. Explore the diverse roots of others who made a new life in Boston on a Chinatown tour, and learn more about the city’s role in the fight to end slavery on a Black Heritage Trail Walking Tour.
Stay at solo-friendly hotels
Boston offers ample accommodations for the solo traveler. For more affordable, centrally located stays, HI Hostel Boston and Meco Pod Hotel have private and shared bunk accommodations. Many of the city’s hotels also offer special winter packages at rates among the lowest of the year.
